My size small Jos A. Bank shoe trees don't get along with my with my size 8.5 Eastland Mocs. The end of the shoe tree pokes the end of the toe box and pushes the leather out of its natural shape.

Is this because the shape of the shoe tree was meant for shoes with pointier ends, or because the shoe tree is too large for the shoe? Are there different types of shoe trees for different types of shoes?

I see conflicting opinions on how shoes should fit lengthwise. The fit guide says you want your toe to just graze the front of the shoe, but most people seem to say you want about 1/2" of room in the toe box.

At 5'8 with a 40" chest I'm having a hard time finding jackets and coats that pass the "hug" test. Mediums usually fit well and feel fine until I bring my arms forward when driving or bend down to tie my shoes.

Can a tailor do anything to these coats? What parts need to be altered for that range of movement? Or is my only option to size up and spend a fortune having everything else brought in?

I use Dr. Marten's Wonder Basalm (Coconut/lanolin/beeswax) on my winter boots; Should I be using it to condition my spring and summer shoes (Sebago camp mocs, Florsheim penny loafers) as well, or something else entirely?